Dry-to-the-touch anaerobically curable compositions and products made therefrom

ABSTRACT

Dry-to-the-touch compositions containing a polymeric matrix and a anaerobically curable component present within the polymeric matrix are disclosed. In a particularly desirable form, the compositions are moisture curable. The compositions are non-flowable, at high temperatures, and have an improved solvent resistance once cured.

RELATED U.S. APPLICATION DATA

This application continues from International Patent Application No.PCT/US2008/006295, filed on May 16, 2008, which claims the benefit of anearlier filing date from U.S. Provisional Application No. 60/939,526,filed May 22, 2007, the disclosures of each of which hereby beingexpressly incorporated herein by reference.

BACKGROUND OF THE INVENTION

1. Field of the Invention

The present invention relates to curable adhesive and sealantcompositions in a dry-to-the-touch form. More particularly, the presentinvention relates to dry-to-the-touch adhesive and sealant compositionswhich are particularly useful in threadlocking and sealing applicationsand may include various product forms of the compositions includingdry-to-the-touch tapes and gaskets.

2. Brief Description of Related Technology

It is common practice in the use of threaded mechanical fasteners, suchas nut/bolt assemblies, to apply to one or more of the threadableengagement surfaces thereof, an adhesive/sealant composition, termed athreadlocking composition, for the purpose of locking and/or sealing theconstituent members of such fasteners when they are engaged in theirfinal interlocked state.

Such threadlocking compositions significantly increased the torquerequired to break or turn the engaged threaded members. Conventionalthreadlocking compositions oftentimes include co-reactive adhesivesystems. With this type of threadlocking composition, two or morecomponents are mixed before applying the resulting composition to thethreaded engagement surface(s) of the fastener on which the componentsin the threadlocking composition react to cure. Examples of suchco-reactive systems include epoxy resin adhesive compositions.

Liquid adhesive compositions have long been used in sealing andthreadlocking applications and have become a standard part of assemblyproduction as well as in the maintenance of machinery, tools and thelike. Among the liquid adhesive compositions commonly used in theseapplications are anaerobic compositions. These compositions provideexcellent threadlocking and sealing properties when cured and thatremain stable, and thus in liquid form, until they are placed betweenparts where they cure in the absence of air. Moreover, thesecompositions remain stable for long periods of time during storage inthe bottle.

In many situations, the ability of the liquid adhesive composition tomigrate from parts is problematic, causing contamination in the generalvicinity, as well as contamination of the environment. One attempt tocreate a convenient ready-to-use threadlocking product has been the useof preapplied adhesive compositions, such as those in micro-encapsulatedform. In such cases, the adhesive composition is applied to the threadedpart, such as a bolt or nut, and remains in the uncured state untilmated. Generally, in this case, components which would cause prematurecuring of the unmated part are kept separated from other components byencapsulation. The mating of the parts causes rupture of theencapsulation casing, thereby releasing the components for cure.

Compositions that are applied to parts just before mating have alsorelied on wax or wax-like matrices into which anaerobic curable resinsare incorporated. While such compositions are easy to apply and havecertain advantages, such as non-flowability due to their rheologicalproperties, they are not dry-to-the-touch. Moreover, such compositionsgenerally lose their non-flowable nature once certain temperatures areexceeded, such as 180° F. or in some cases involving polyamide matricesthose temperatures may reach 260° C. (500° F.) before that happens, andthus lose their advantage over pre-applied or traditional liquid threadlockers since at these temperatures migration begins to occur. Moreover,the wax or wax-like matrices have been described as being used insignificantly smaller amounts than the anaerobic component such asamounts of up to about 20% by weight of the total compositions.

While preapplied coatings have many advantages, special processing issometimes required to prepare and apply the adhesive coatings inadvance. Such compositions are not always useful on an as-needed basis,such as when an immediate need for application of a curable compositionis required. For instance, it may be necessary to stock and inventorydifferent sizes of pre-applied coated parts in advance. Thus,pre-applied coatings do not solve the problem for many applicationsrequiring ready-to-use compositions.

Though conventional anaerobic threadlockers have been and remainwell-received in the marketplace, there are shortcomings for certaincommercial applications that have been observed with the use ofconventional liquid anaerobic threadlockers, as well as knownnon-flowable, thixotropic anaerobic-based threadlockers. For instance,oftentimes such compositions do not fully cure through large gaps. Also,because of their nature of anaerobic cure, portions of the adhesivewhich remain exposed to air once applied to the parts will havedifficulty curing (absent a secondary cure mechanism that is triggered).Thus, external bondlines which remain exposed to air on a nut/boltassembly oftentimes will remain liquid unless additional additives andcure measures are taken to ensure cure. As a result, liquid compositionsat the external bondlines tend to migrate. In the case of conventionalnon-flowable compositions, which depend on the thixotropic and/orrheological properties of the composition for their non-flowability,these compositions will flow if the temperature to which they areexposed is high enough. Additionally, the resistance to solvents ofcured products (that have portions which remain uncured, as noted above)may be poor, indicative of questionable integrity when environmentalinteraction occurs. This may lead to contamination problems andhazardous conditions for the surroundings.

It would be extremely useful and a significant advance in the field ofreactive threadlockers and sealants, to provide a reactive formulationuseful for threadlocking applications, which overcomes the disadvantagesof known compositions. It would also be highly advantageous to provide acost effective dry-to-the-touch, easy to apply composition, as analternative to such known threadlocking compositions.

SUMMARY OF THE INVENTION

The present invention relates to a composition useful for adhesivelyfixturing matably engageable structural elements, such as threadlockingor nut/bolt assemblies, so that the structural elements are adhesivelybonded and sealed upon their being engaged in a final interlocked state.The present invention broadly relates to a co-reactive adhesive/sealantcomposition, having utility for threadlocking matably engageablesurfaces of threaded mechanical fasteners, or adhesive bonding of othermatably engageable structural elements.

The present invention relates to dry-to-the-touch compositions whichinclude a polymeric matrix and an anaerobically curable componentdispersed within the polymeric matrix, where the polymeric matrix shouldbe present in amounts of about 30% to about 80% by weight of thecomposition and the composition itself remains non-flowable attemperatures greater than 260° C. up to about 300° C. The polymericmatrix may include materials selected from polyurethanes, polyureas,polysulfonamides, polythiourethanes and combinations thereof.

In some aspects of the invention, a polyurethaneurea may be used incombination with one or more of the polymeric matrices mentioned above.In other aspects of the invention, a polyurethaneurea polymeric matrixmay be used as the sole or primary polymer in the matrix. Here, thepolyurethaneurea may be present in an amount of about 30% to about 80%by weight of the total composition. Compositions employing apolyurethaneurea in the polymeric matrix, either alone or in combinationwith other polymers in the matrix, also remain non-flowable attemperatures greater than 260° C. up to about 300° C.

The inventive compositions are dry-to-the-touch and may include morethan one cure mechanism, e.g. a dual cure system. The polymer matrix mayserve as a carrier for the anaerobically curable composition or theremay be a separate carrier on which the inventive compositions are formedand reside prior to end use. For example, in some instances a filmsubstrate may be used as a separate carrier for the inventivecompositions which may be deposited in tape form on the film substrate.

In some aspects of the invention, the curable polymeric matrix mayundergo a secondary cure stage. For example, the presence of residual orlatent reactive groups on the cured polymeric matrix permits furthercure, and in some instances, reaction with the anaerobic component.

The anaerobically curable composition includes a (meth)acrylate, and afree radical initiator, such as a peroxide or a perester. Theanaerobically curable component serves to provide sealant andthreadlocking properties for the composition. In the context of thepresent invention, the anaerobically curable composition is distributedwithin the polymeric matrix. The resulting composition may then beapplied to an inert carrier substrate, such as a film or strip, andafter exposure to conditions sufficient to cure, the polymeric matrixportion of the composition cures to a dry-to-the-touch film or coating.The anaerobically curable compositions within the polymeric matrix arethen cured once conditions conducive to anaerobic cure are attained.

The compositions of the present invention are less messy, do not drip,may be applied to parts and stored prior to use have large gap-fillingcapabilities, and may be easily transported in a portable form, such asa toolbox, in large part due to their dry-to-the-touch nature, evenprior to anaerobic cure.

The present invention may also be used to create articles ofmanufacture, such as tapes, films, strips, gaskets, pads, strings, andvarious other shaped pieces, which may be applied to a threaded part,such as a nut or a bolt, or other substrates, the anaerobic portionremaining uncured until subjected to conditions suitable for anaerobiccure, such as the exclusion of air by the mating of parts. Thecompositions may also be useful in various sealing and pottingapplications.

As noted above, another advantage of the inventive compositions includesthe ability to be used in large gap applications, at which knownanaerobically curable compositions are not well-equipped to succeed.Conventional anaerobically curable compositions are stabilized in thepresence of oxygen or air, and as such do not effectively cure at theedge of the mating parts, because that location is oftentimes exposed toair. This results in the potential for uncured material to remain evenafter the mating parts are adhesively secured. The uncured compositionis free to migrate, contaminate its surroundings and can createdifficulties in product quality and increase manufacturing costs.Heretofore, this disadvantage had been remedied through the use of asecondary cure system, such as light cure, to seal that exposed portion.However, these disadvantages are overcome by the inventive compositionsbecause the products formed therefrom, e.g., threaded parts having theinventive composition applied thereon, are all dry-to-the-touch and donot melt or soften unless subjected to high temperature. The curedpolymeric matrix may serve to prevent the anaerobic component frommigrating by effectively trapping it within the matrix.

In another aspect of the invention, compositions are provided in whichan anaerobically curable component is distributed within a curablepolymeric matrix. The polymeric matrix may be formed by the reaction ofa polyisocyanate reactant with at least one compound selected from amultifunctional alcohol, a polyamine and a polythiol, to form adry-to-the-touch product. In another aspect of the invention, acomposition is provided in which the reaction product includes ananaerobically curable composition distributed within a cured polymericmatrix.

In another aspect of the invention, a product is provided in which acarrier substrate is coated with a composition of the invention. Thecoating includes an anaerobically curable component present within acurable polymeric matrix. Desirably, the polymeric matrix is moisturecurable, which upon exposure to moisture cures to a dry-to-the-touchcoating or film, and which can further be cured anaerobically at a latertime. Moisture cure of the polymeric matrix may be accelerated by thepresence of moisture cure catalysts and/or moisture-containingcomponents.

In another aspect of the invention, a method is disclosed for preparinga composition. The composition is prepared by first providing a mixtureof a moisture curable composition and an anaerobically curablecomposition, then exposing the mixture to conditions of moisture to curethe moisture curable composition to form a cured dry-to-the-touch matrixcontaining the anaerobically curable composition distributed therein.The mixture may contain reactants from which form a material selectedfrom polyurethanes, polyureas, polysulfonamides, polythioureas andcombinations thereof. The mixture may also contain reactants which formpolyurethaneureas. These reactants may include any of those describedherein.

In another aspect of the invention, an article of manufacture isdisclosed. The article includes a matable member, such as a threadedmember at least partially coated with the dry-to-the-touch compositionof the invention. The dry-to-the-touch composition includes ananaerobically curable component distributed in a polymeric matrix.Desirably, the threaded member is a nut, bolt, flange, gear or similararticle. A variety of product forms may be formed and in some instancesprecut from the cured polymeric matrix.

Other articles, such as gaskets, may be formed from the inventivecompositions.

The invention also provides a method for preparing an article ofmanufacture, the steps of which include providing a threaded member andat least partially coating the threaded member with a polymeric matrixhaving an anaerobically curable component distributed therein.Desirably, the polymeric matrix is at least partially cured, and moredesirably, substantially cured. Regardless of whether the matrix ispartially or substantially cured, the composition in which it is used isdry-to-the touch.

In another aspect of the invention, a method of assembling threadedparts is provided. The method includes the steps of providing a firstthreaded member, providing a second threaded member capable of matinglyengaging said first threaded member; at least one of the first andsecond threaded members being at least partially coated with adry-to-the-touch composition including a polymeric matrix and ananaerobically curable component distributed therein, and matinglyengaging the first and second threaded parts and permitting thecomposition to anaerobically cure therebetween.

The compositions of the invention may be formulated into one and twopart systems, depending on choice.

In one aspect of the invention, there is provided a compositionincluding a first part including a curable composition including adiisocyanate and optionally a polyol, a polyamine, a polythiol andcombinations thereof; and a second part including: a curable compositionincluding: an anaerobically curable resin; an anaerobic cure system; anda polyol. In some embodiments, the diisocyanate may be a polymericdiisocyanate.

In other aspects of the invention, there is provided a compositionincluding: a first part including the cured reaction product of one ormore of the following: a diisocyanate and a polyol; a diisocyanate and apolyamine; a diisocyanate and a thiol; a diisocyanate, a polyol and apolyamine; and a second part including an anaerobically curablecomponent.

In other aspects of the invention, there is provided a compositionincluding: a first part including: a diisocyanate; and a second partincluding: an anaerobically curable component; and at least one of thefollowing: a polyol; a polyamine; a polythiol; a polyol and a polyamine.

In some aspects of the invention, there is disclosed an article ofmanufacture including a threaded member partially coated with adry-to-the-touch composition. The article of manufacture may include apreformed gasket. In some embodiments, the article of manufacture mayinclude a dispenser for containing a dry-to-the-touch composition. Thedispenser may include two or more chambers for dispensing first andsecond parts of the inventive composition. The dispenser may alsoinclude a static mixing nozzle for mixing the first and second parts. Inaddition, the dispenser may include a plunger for advancing the contentsof the first and second parts within their respective chambers.

In other aspects of the invention, there is provided a method of sealingthreaded parts including: providing a first threaded member; providing asecond threaded member capable of matingly engaging with the firstthreaded member; at least one of the first and second members being atleast partially coated with a composition including: a first partincluding a curable composition including: a diisocyanate and optionallya polyol, a polyamine and a polythiol; and a second part including acurable composition including: an anaerobically curable resin; ananaerobic cure system; and a polyol; and (c) matingly engaging the firstand second threaded members and permitting the composition toanaerobically cure therebetween.

DETAILED DESCRIPTION OF THE INVENTION

The present invention broadly relates to a reactive adhesive/sealantcomposition, having utility for threadlocking matable engagementsurfaces of threaded mechanical fasteners, or adhesive bonding of othermatably engageable structural elements. Compositions of the presentinvention, in general, include a polymeric matrix and an anaerobicallycurable component within the polymeric matrix.

The term “curing”, or “cure” as used herein, refers to a change instate, condition, and/or structure in a material, as well as, partialand complete curing.

As used herein, the term “(meth)acrylate” is intended to includemethacrylates and acrylates.

The term “partially cured” indicates that some portion of the reactivegroups remain unreacted. The term “substantially cured” indicates anegligible amount, if any, of the reactive groups remain unreacted. Theunreacted groups may further participate in reacting with the anaerobiccomposition or other components present in a subsequent polymerization.

The term “dry-to-the-touch” indicates that the composition hassufficiently solidified or cured such that when a cotton swab is gentlytouched to the surface of the polymeric matrix, no adherence of the swaboccurs. The term “dry-to-the-touch time” indicates the time necessary toachieve a dry-to-the-touch state.

The term “tack-free” indicates the surface of the composition does notstick to a high-density polyethylene disposable pipette when the pipettegently touches the surface of the material. The term “tack-free time”indicates the time necessary to reach a tack-free state.

Polymeric Matrix

The polymeric matrix may include a polymer selected from polyurethanes,polyureas, polysulfonamides, polythiourethanes or any combinationsthereof. The polymeric matrix may also include polyurethaneureas aloneor in combination with other polymers. The polymer may be dried or curedto trap therein the anaerobically curable component which has beendistributed therethrough. This results in a dry-to-the-touch compositionthat still has the ability to anaerobically cure when subjected toconditions conducive to anaerobic cure. As previously mentioned, thepolymeric matrices allow for large gap filling, such as 50 mm to 500 mmor greater, due to the ability of the cured matrix to retain theunreacted liquid anaerobic resin and anaerobic cure system without lossto the surrounding environment of unreacted components. Thus, even verylarge gap applications remain dry-to-the-touch. Moreover, parts such asstand-alone gaskets may be made from the compositions, which can then beplaced between parts and allowed to further cure anaerobically. Once thepolymeric matrix of the inventive compositions is cured, a non-flowablestate for the composition is reached. In some embodiments, depending onthe choice of polymer matrix, the matrix remains dry-to-the-touch up totemperatures of 400° C. (752° F.). Generally, the compositions remaindry-to-the-touch and non-flowable at temperatures greater than 260° C.(500° F.) and desirably greater than 300° C. (572° F.).

The polymeric matrix itself has a melting or softening point greaterthan 260° C. Desirably the polymeric matrix has a melting or softeningpoint greater than 300° C. In some embodiments the melting point orsoftening point is between about 300° C. and about 400° C. Thus, theinventive compositions are non-flowable at temperatures considerablyhigher than known anaerobic threadlockers having the anaerobic curablecomponent in a carrier or matrix.

The polymeric matrix, which is responsible for the dry-to-the-touchproperty of the inventive compositions, is desirably present in amountsof about at least 30% by weight, and desirably about at least 50% byweight of the total composition and may be present in amounts of about80% by weight.

Examples of useful polyurethanes include those compounds having arepeating unit such as,

where X is an aliphatic or aromatic hydrocarbyl or heterohydrocarbyldiradical group or chain and n is 1-4. R¹ is an alkylenyl or an arylenylgroup.

Other useful polyisocyanates include polymeric polyisocyates such asthose conforming to the general structure:

where R in each occurrence may be the same or different and may be ahydrocarbyl group or hetero hydrocarbyl diradical and n is 1-20.

The polyurethanes useful as the polymeric matrix may be formed from thereaction product of an isocyanate and an alcohol. Examples of usefulpolyisocyanates include those that correspond to the following formula:

OCN—X—NCO

where X in each occurrence may be the same or different and is a C₁₋₂₀hydrocarbon or heterohydrocarbon diradical. Desirably, X is an alkyleneor an arylene diradical.

For example, useful isocyanates for forming the reaction product(s)include polyisocyanates such as monomeric 4,4′-methylene diphenyldiisocyanate (“MDI”), phenyl diisocyanate, toluene diisocyanate (“TDI”),4,4′-diphenyl diisocyanate, 4,4′-diphenylene methane diisocyanate,dianisidine diisocyanate, 1,5-naphthalene diisocyanate, 4,4′-diphenylether diisocyanate, p-phenylene diisocyanate, 4,4′-dicyclo-hexylmethanediisocyanate, 1,3-bis-(isocyanatomethyl)cyclohexane, cyclohexylenediisocyanate, tetrachlorophenylene diisocyanate,2,6-diethyl-p-phenylenediisocyanate, and3,5-diethyl-4,4′-diisocyanatodiphenylmethane. Still otherpolyisocyanates that may be used are polyisocyanates obtained byreacting polyamines containing terminal, primary and secondary aminegroups or polyhydric alcohols, for example, the alkane, cycloalkane,alkene and cycloalkane polyols such as glycerol, ethylene glycol,bisphenol-A, 4,4′-dihydroxy-phenyldimethylmethane-substitutedbisphenol-A, and the like, with an excess of any of the above-describedisocyanates.

Useful alcohols for reacting with the polyisocyanate to form thepolyurethanes include, without limitation, polyethyl glycol ethershaving 3-7 ethylene oxide repeating units and one end terminated with anether or an ester, polyether alcohols, polyester alcohols, as well asalcohols based on polybutadiene. One particularly useful alcohol is1,4-butanediol. Additional useful alcohols include, without limitation,castor oil, glycerin, polyethylene glycol, etherdiol, ethylene glycol,caprolactone polyols and combinations thereof.

The specific type of alcohol chosen and the molecular weight range canbe varied to achieve the desired effect. Generally, polyhydroxycompounds, straight or branched chain aliphatic or cyclic primary orsecondary alcohols containing C₅₋₂₅ may be used.

Examples of useful polyureas in the present invention include, withoutlimitation, those compounds including the repeating unit

where Y and R are hydrocarbon or heterohydrocarbon diradicals and n is1-20.

The polyureas useful as the polymeric matrix may be formed from thereaction product of an isocyanate and an amine. Examples of usefulpolyisocyanates may include any of those as listed above.

Useful amines include aliphatic or aromatic amines. Desirably polyaminesare particularly useful. Desirable aliphatic amines include polyethyleneglycol ether amines. Desirable aromatic amines include those havingpolyethylene glycol ether substitution on the aromatic ring.

For example, commercially available amines sold under the tradenameJEFFAMINE by Huntsman Corporation, Houston, Tex., may be employed.Examples include JEFFAMINE D-230, JEFFAMINE D-400, JEFFAMINE D-2000,JEFFAMINE T-403, JEFFAMINE ED-600, JEFFAMINE ED-900, JEFFAMINE ED-2001,JEFFAMINE EDR-148, JEFFAMINE XTJ-509, JEFFAMINE T-3000, JEFFAMINET-5000, and combinations thereof.

The JEFFAMINE D series are diamine based products and may be representedby:

where x is about 2.6 (for JEFFAMINE D-230), 5.6 (for JEFFAMINE D-400)and 33.1 (for JEFFAMINE D-2000), respectively.

The JEFFAMINE T series are trifunctional amine products based onpropylene oxide and may be represented by:

where x, y and z are set forth below in Table A.

TABLE A JEFFAMINE Approx. Mole Product Initiator (A) Mol. Wt. PO T-403Trimethylolpropane 440 5-6 T-3000 Glycerine 3,000 50 T-5000 Glycerine5,000 85

More specifically, the JEFFAMINE T-403 product is a trifunctional amineand may be represented by:

where x+y+z is 5.3.

The JEFFAMINE ED series are polyether diamine-based products and may berepresented by:

where a, b and c are set forth below in Table B.

TABLE B JEFFAMINE Approx. Value Approx. Product B a + c Mol. Wt. ED-6008.5 2.5 600 ED-900 15.5 2.5 900 ED-2001 40.5 2.5 2,000

As used herein, the terms “polyurethaneurea” and “polyureaurethane” areinterchangeable. Examples of useful polyurethaneureas include thereaction products of the reaction of diols and diamines withdiisocyanates. These reactants may be selected from a wide variety ofmaterials including those described previously for their respectiveclasses.

Examples of useful polysulfonamides include those formed from thereaction product of isocyanates with compounds having the generalstructure of

where R′ and R″ are hydrocarbyl or heterohydrocarbyl groups. An exampleof a sulfonamide is the composition formed by the reaction of saccharinwith isocyanate.

The polythiourethanes useful as the polymeric matrix may be formed fromthe reaction product of a polyisocyanate and a polythiol. Examples ofuseful polyisocyanates may include any of those listed herein. Examplesof useful polythiols include those which have an available —SH group.For example, useful polythiols for forming the reactant product includepentaerythritol tetrakis [3-mercaptoproprionate], among others.

The polymeric matrices allow the compositions to be used on a variety ofsurfaces including ferrous-containing surfaces, non-ferrous metals suchas stainless steel, zinc phosphorous coated surfaces, other passivemetal surfaces, wood and plastics. Whereas conventionalanaerobically-curing threadlockers generally require the presence of aferrous-containing surface for cure, the inventive compositions aresurface insensitive due to the polymeric matrix, which will cure onvirtually any surface and in the presence of air.

Anaerobic Compositions

The anaerobically curable composition which is distributed within thepolymeric matrix may be chosen from any number of anaerobiccompositions. Compositions useful include an anaerobically curablecomponent such as a (meth)acrylate monomer or oligomer and a freeradical initiator, such as a peroxide.

Examples of useful (meth)acrylates include, monomers such as,monomethacrylates, dimethacrylates, trimethacrylates andtetramethacrylates. (Meth)acrylate monomers suitable for use hereininclude hydroxypropyl (meth)acrylate (“HPMA”), hydroxyethyl(meth)acrylate (“HEMA”), cyclohexyl (meth)acrylate, tetrahydrofuran(meth)acrylates, glycidyl (meth)acrylates, cyanoethyl (meth)acrylate,hexanediol di(meth)acrylate, polyethylene glycol di(meth)acrylates,diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate(“TRIEGMA”), tetraethylene glycol di(meth)acrylate, dipropylene glycoldi(meth)acrylate, di-(pentamethylene glycol) di(meth)acrylate,tetraethylene diglycol di(meth)acrylate, neopentyl glycol diacrylate,tetramethylene di(meth)acrylate, ethylene dimethacrylate, bisphenol-Adi(meth)acrylates, such as ethoxylated bisphenol-A (meth)acrylate(“EPIBMA”), trimethylol propane tri(meth)acrylate, trimethylol propanetriacrylate and diglycerol tetra(meth)acrylate.

Of course, combinations of these (meth)acrylate monomers may also beused.

In one embodiment, the (meth)acrylate has the general structural formulaII.

H₂C═CGCO₂R²  (II)

where G may be hydrogen, halogen or alkyl of 1 to about 4 carbon atoms,and R² may be selected from alkyl, cycloalkyl, alkenyl, cycloalkenyl,alkenyl, aralkyl or aryl groups 6 to about 16 carbon atoms, any of whichmay be optionally substituted or interrupted as the case may be withoxygen, halogen, carbonyl, hydroxyl, ester, carboxylic acid, urea,urethane, carbonate amine, amide, sulfur, sulfone and the like.

In another, particularly desired embodiment, the (meth)acrylates havegeneral structural formula III:

where R² may be selected from hydrogen, alkyl of 1 to about 4 carbonatoms, hydroxyalkyl of 1 to about 4 carbon atoms or

R³ may be selected from hydrogen, halogen, and alkyl of 1 to about 4carbon atoms;

R⁴ may be selected from hydrogen, hydroxy and

m is an integer equal to at least 1, e.g., from 1 to about 8 or higher,for instance, from 1 to about 4;

n is an integer equal to at least 1, e.g., 1 to about 20 or more; and

v is 0 or 1.

The (meth)acrylate should be present in the compositions within therange of from about 1 percent by weight to about 60 percent by weight,desirably from about 5 percent by weight to about 50 percent by weight,such as from about 10 percent by weight to about 40 percent by weight,based on the total composition.

Examples of useful peroxides which may be incorporated in the presentinvention, include without limitation, hydroperoxides such as cumenehydroperoxide (“CHP”), t-butylhydroperoxide (“TBH”), p-menthanehydroperoxide, diisopropylbenzene hydroperoxide, pinene hydroperoxide,methyl ethyl ketone hydroperoxide, and tertiary butyl perbenzoate.

In one desirable aspect of the invention, the polymeric matrix may cureby moisture and thus, a moisture cure catalyst may be included to speedand/or enhance the cure. Examples of useful moisture cure catalystsinclude organo-metal catalysts including titanates such astetraisopropylorthotitanate and tetrabutoxyorthotitanate, as well asmetal carboxylates such as dibutyltin dilaurate, dibutyltin dioctoateand the like.

Useful moisture cure catalysts include metal salts typically selectedfrom titanium, tin, zirconium and combinations thereof. Nonlimitedexamples of moisture cure catalysts include, for example, dibutyltindilaurate, dibutyltin diacetate, dibutyltin dioctoate, dibutyltinmaleate, dialkyl tin hexoate, dioctyltin dilaurate, iron octanoate, zincoctanoate, lead octanoate, cobalt naphthenate, tetrapropyltitanate andtetrabutyltitanate. Other useful moisture cure catalysts, such as thosedisclosed in U.S. Pat. No. 4,111,890, may also be employed and areherein incorporated by reference.

Other conventional catalysts can also be incorporated into the presentinvention. For example, the inventive compositions also include anaddition cure catalyst. Suitable addition cure catalysts that can beused with the present compositions include platinum-based ones, such asplatinum-siloxane complexes, which facilitate hydrosilation reactions.The moisture cure catalyst should be used in an amount sufficient toeffectuate moisture cure, which desirably is in the range of about 0.1to about 10% by weight. Elevated temperatures may also be used to curethe inventive compositions of the present invention. Photoinitiators,such as visible and UV initiators, may also be incorporated.

Another embodiment of the invention may include a cured polymeric matrixand an uncured anaerobically curable composition. The cured polymericmatrix may include a material selected from polyurethanes, polyureas,polysulfonamides and combinations thereof, examples of which arediscussed above. The cured polymeric matrix may also be made from orinclude polyurethaneureas. The cured polymeric matrix may include areaction product of a polyisocyanate with at least one of the following:an polyalcohol, an polyamine or a polythiol, examples of which arediscussed herein. The cured polymeric matrix may be a moisture curablecomposition, examples of which are discussed above. The uncuredanaerobically curable composition which is distributed within thepolymeric matrix may be chosen from any number of anaerobiccompositions. For example, the uncured anaerobically curable compositionmay include a (meth)acrylate and a peroxide, examples of which arediscussed herein.

Pre-formed articles made from the compositions of the present inventionmay include tapes having a substrate carrier, such as a film, and acoating which includes the compositions of the invention. Useful tapesubstrate carriers include plastic, cellulosic, cotton or polyurethanefilms. The tape substrate may be in the form of a tape, a string, asheet or film. Useful polymeric matrixes and anaerobically curablecomponents are described above. Pre-coated articles include matablyengageable substrates, such as threaded parts. The inventivecompositions may be applied to these parts and cured, desirably bymoisture, to a dry-to-the-touch coating or film which is further capableof anaerobic cure once assembled with a matable part. Alternatively, apre-formed dry-to-the-touch film may be formed and then applied to asubstrate. The coated substrate may then undergo anaerobic cure whenexposed to appropriate anaerobic conditions. Other preformed articlesmay be formed which can undergo further anaerobic curing. For example,gaskets may be formed from the inventive compositions which can then beplaced between mating surfaces and anaerobically cured.

EXAMPLES Example I

A one part anaerobic adhesive, sold by Henkel Corporation asThreadlocker 2760, was used to make a two-part adhesive composition.These parts are described in Table I. Both parts were then mixedtogether to form the final composition. The final composition was thenused to coat a substrate, such as cellophane tape, Teflon tape, andcotton string and allowed to room temperature moisture cure for 24 hoursto produce a dry-to-the-touch composition. The final composition wasalso applied as a thin film coating to a polyethylene substrate andsimilarly cured. The cured films were then peeled from their respectivesubstrates and applied to the threads of the bolts. The bolts were thenmatched with the nuts, the assembly was pretorqued to 40 in/lb and thenallowed to room temperature anaerobic cure for 24 hours.

TABLE I Inventive Composition A COMPONENT % WT PART ONE EBIPMA 72.00PEGMA 22.50 Saccharin 1.000 Stabilizers 0.500 Dyes 0.500 Accelerator(actyl phenylhydrazine (APH)) 0.500 Thickener (silica) 2.000 CHP (cumenehydroperoxide) 1.000 100.00 PART TWO Baytec* MP020 100.00 *pre-reactedpolymeric methylene diisocyanate having low free isocyanate content.

The composition as set forth in Table I, was applied to nuts and boltsin two equal amounts comprised of degreased steel and oily zincphosphate fasteners (nuts and bolts).

The initial breakloose torque was recorded and is shown in Table I.Breakloose-torque is the torque strength needed to unlocked threadedparts which were assembled together by applying anaerobic adhesives onfasteners followed by pretorquing with 40 inch-pounds force. Such aforce generally results in all threaded surfaced being mated, and thebreakloose-torque test is a useful test for threadlocking materials onassembled products. A relatively high breakloose torque is preferred asthis is the force required to initially move the nut. A relatively lowerprevail strength is desired to provide ease of disassembly. The resultsof these tests are shown in Table I.

TABLE II Breakloose Torque Strength at 24 h/RT (in. lbs.) SubstrateControl* Inventive Composition A String 62 128 Clear tape 33 141 Teflontape 47 135 Paper 74 77 Dry thin film N/A 124 *Substrate withoutcoating.

As shown in Table II, the high breakloose values of the inventivecompositions indicate that the composition has anaerobically curedsubsequent to the mating of the parts.

Inventive composition A was also tested on zinc phosphate coated steelnuts and bolts which were also coated with oil. For comparativepurposes, the same type of nuts and bolts were tested without anyadhesive product as well as with commercially available Threadlocker2760. The results shown below indicate a breakloose which issignificantly greater than nuts and bolts without any product, but lowerthan the standard liquid anaerobic product.

TABLE III Product Used Type Test Substrate Nuts and Bolts In.-Lbs. NoneBreakloose None Phos + Oil Steel 41 Inventive Breakloose None Phos + OilSteel 237 Composition A 2760 Breakloose None Phos + Oil Steel 451

The nut and bolt assemblies were also observed for any uncured materialat the external bondlines and none were found to be present. Theexternal bondlines were dry-to-the-touch.

Example II

Table IV below is another example of a two-part dry-to-the-touchcomposition capable of further anaerobic cure in accordance with theinvention. The presence of PEGMA in the first part facilitates mixingand its physical presence serves to control the speed of reaction of thefree isocyanate groups in the monomeric MDI.

TABLE IV Inventive Composition B COMPONENT % by weight CAS No. PART ONEMonomeric 4,4′-MDI 70-100 26447-40-5 Polyethyleneglycol 0-30 110-82-7,123-31-9 Dimethacrylate (PEGMA) PART TWO Polyethyleneglycol 1-30110-82-7, 123-31-9 Dimethacrylate Castor based organic thixotrope 1-3 8001-78-3 Castor oil 20-40  8001-78-3 1,4 Butanediol 5-15 110-63-4 Poly(acrynonitrile-butadiene- 5-20 100-42-5, 9003-56-9 styrene) Saccharin1-2  81-07-2 Polyethelene powder 0.1-.5  9002-88-4 Cumene hydroperoxide0.5-2.0  80-15-9 Glycerine 1-6  56-81-5 Polyoxypropylenediamine 5-109046-10-0

Parts One and Two of Composition B were mixed in a 1:2 ratio (PartOne:Part Two). The resulting mixture was then applied as a thin filmcoating on a substrate and allowed to cure to room temperature for 24hours to produce a dry-to-the-touch composition. The combination wasalso applied as a thin film coating to a polyethylene substrate andpeeled from the polyethylene substrate to form a dry-to-the touch thinfilm after 24 hours of room temperature curing. Uncoated tape substratesand the tapes coated with the inventive compositions were applied tothreaded bolts (zinc phosphate, oily steel ⅜×16). The bolts were thenmated with nuts (zinc phosphate, oil steel ⅜×16) and allowed to cure 24hours at room temperature. The results of the performance of thecomposition when placed on a variety of different substrate carriers areshown in Tables V and VI.

The initial breakloose-torque was recorded and is shown in Table V.Breakloose-torque is the torque strength needed to disassemble threadedparts which were assembled together by applying the compositions onfasteners followed by pretorquing with 40 inch-pounds force. The initialbreakaway-torque in inch-pounds was recorded and is shown in Table V.Breakaway-torque is the torque strength needed to unlock threaded partswhich were hand assembled together without pretorque using an anaerobicadhesive.

TABLE V Breakloose/Prevail Torque at 24 h(in. lbs.) Substrate Control*Inventive Composition A Teflon tape   47/25.4 135/36 Cotton string 39/11128/42 Clear tape 33/8  141/20 Paper strip 43/15 275/32 Dry thin filmN/A 124/25 *Substrate without coating

TABLE VI Breakaway/Prevail Torque at 24 h (in.-lbs.) Substrate Control*Inventive Composition A Teflon tape 0/0 95/36 Cotton string 35.4/17.428/39 Paper strip 38/19 139/201 Dry thin film N/A 456/281 *Substratewithout coating

As indicated in the results in Tables V and VI, the inventivecompositions show significant improvement with respect to the differencebetween breakloose and prevail strengths where the breakloose strengthwas advantageously greater than the prevail strength, as compared tosubstrate tape alone.

The nut and bolt assemblies were also observed for any uncured materialat the external bondlines and none were found to be present. Theexternal bondlines were dry-to-the-touch.

Example III

Inventive Composition A was also formulated as a one-part system. Inthis embodiment, all components were mixed together at the time of use.In some embodiments of the one-part system, one or more highly reactivecomponents such as diisocyanates, polyamines, polythiols or polyols maybe encapsulated or otherwise physically or chemically treated to makethem remain unreactive until needed. For example, protective groups maybe chemically incorporated to tie-up the highly reactive moiety. Suchgroups may later be removed, such as by heat or other chemical means,when cure is desired. Other means of preventing their premature reactionmay include physically separating them by coatings or other matriceswhich when ruptured release the component for reaction.

Inventive compositions C-F were made using the formulations as shown inthe following Tables VII-X.

Example IV

Example IV was prepared according to the formulation set forth in TableVII below.

TABLE VII Inventive Composition C COMPONENT % by weight PART ONELupranate MP 102* 78.65 Lupranate M20S* 10.00 Anaerobic catalyst(Saccharin) 0.30 Plasticizer (Triacetin) 10.00 Tertiary butylperoxybenzoate (TBPB) 1.00 Defoaming agent 0.05 Total 100.00 PART TWOPEGMA 25.00 HPMA 1.00 Thickener 0.50 Tetrafunctional polyether polyol48.00 Castor Oil (Low moisture polyol) 24.39 Dye 0.04 Defoaming agent0.05 Dibutyltin dilaurate (DBTDL) 0.02 Anaerobic catalyst(Triethanolamine) 1.00 Total 100.00 *Lupranate MP 102 and M20S arepolymeric methylene diisocyanates of different viscocities.

Procedure for Preparing Composition C:

The first three components of Part One were added to a clean dry mixingvessel and mixed under a nitrogen blanket for approximately 15 minutes.The remaining components were added to the mixture. Once all thecomponents were combined, the mixture was mixed for 30 minutes under anitrogen blanket. A vacuum was applied to the mixture until it wasdeaerated.

The first six components of Part Two were added to a clean dry mixer andheated to approximately 65° C.-70° C. for about 1 hour under fullvacuum. The mixture was then cooled to 45° C. The remaining componentswere added to the mixture and vacuumed for deaeration.

Example V

Example V was prepared according to the formulation set forth in TableVIII below.

TABLE VIII Inventive Composition D PART ONE COMPONENT % by weightAnaerobic catalyst (Saccharin) 0.30 Glycol triester plasticizer(Triacetin) 10.00 Lupranate MP 102 65.36 Castor Oil (Low moisturepolyol) 8.28 DBTDL 0.01 Lupranate M20S 15.00 TBPB 1.00 Defoaming agent0.05 Total 1.000 PART TWO COMPONENTS % by weight PEGMA 25.00 HPMA 1.00Thickener 1.50 Polyol 38.54 Castor Oil (low moisture polyol) 32.85Triethanolamine 1.00 Dye 0.04 Defoaming agent 0.05 DBTDL 0.02 Total100.00

Procedure for Preparing Composition D:

Part one components 1 and 2 were added to a clean, dry reactor which wasflushed with nitrogen. Agitation was started and components 3-5 wereadded. The mixture was mixed for approximately 10-15 minutes. Heat wasapplied to the mixture and maintained at a temperature of approximately55° C.-65° C. for about 1 hour under a nitrogen blanket. The mixture waschecked for isocyanate content. Component 6 was then added while themixture was cooling. Components 7 and 8 were added and the mixture wasmixed for approximately 5 minutes. A vacuum was applied to the mixtureuntil completely degassed.

Part two components 1-7 were added to a clean, dry reactor and agitatedfor approximately 10-15 minutes. Heat was applied and maintained at atemperature of approximately 70° C.-75° C. for about 1 hour under fullvacuum. Moisture content of the mixture was checked. The mixture wasthen cooled to approximately 40° C.-45° C. The remaining components, 8and 9, were added to the mixture and mixed for approximately 5 minutes.A vacuum was applied to the mixture until completely degassed.

Example VI

Example VI was prepared according to the formulation set forth in TableIX below.

TABLE IX Inventive Composition E COMPONENTS % by weight PART ONETriacetin 13.00 Lupranate MP 102 86.95 Defoaming agent 0.05 Total 100.00PART TWO PEGMA 25.00 Castor Oil (low moisture polyol) 32.85 Saccharin0.30 Thickener 1.00 Triethanolamine 1.50 Polyol 43.85 Free-radicalstabilizer 0.75 Chelator 1.00 Dye 0.04 Defoaming agent 0.04 DBTDL 0.02TBPB 0.05 Total 100.00

Procedure for Preparing Composition E:

Part one components 1-3 were added to a clean, dry reactor, which wasflushed with nitrogen. The mixture was mixed for approximately 30minutes under a nitrogen blanket. The completed mixture was dischargedunder nitrogen.

Part two components 1-4 were added to a clean, dry reactor and agitatedfor approximately 10-15 minutes. Components 5-9 were added to themixture in their respective order. Heat was applied to the resultingmixture and maintained at a temperature of approximately 65° C.-70° C.for about 1 hour under full vacuum. The mixture was then cooled toapproximately 45° C. The remaining components, 10-12, were added to themixture and mixed for approximately 5 minutes. A vacuum was applied tothe mixture until it was deaerated.

Example VII

Example VII was prepared according to the formulation set forth in TableIX below.

TABLE X Inventive Composition F PART ONE COMPONENT % by weight LupranateMP 102 100.00 Total 100.00 PART TWO COMPONENTS % by weight PEGMA 25.00Triacetin 10.00 Saccharin 0.30 Thickener 1.00 Castor Oil (low moisturepolyol) 12.50 Triethanolamine 1.50 Polyol 47.35 Free-radical stabilizer0.75 Chelator 1.00 Dye 0.04 Defoaming agent 0.04 TBPB 0.50 DBTDL 0.02Total 100.00

Procedure for Preparing Composition F:

Part two components 1-9 were added to a clean, dry reactor and heated toa temperature of approximately 65° C.-70° C. for about 1 hour under fullvacuum. The mixture was then cooled to approximately 45° C. Theremaining components, 10-13, were added to the mixture as it was mixing.A vacuum was applied to the mixture until degassed.

Example VIII

Inventive compositions C and D were subjected to an evaluationsubsequent to cure of the total composition to determine whether and towhat extent the cured composition resisted exposure to various solventsunder varying conditions.

In Tables XI and XII below, inventive composition C and D were spreadonto aluminum substrates and cured, at room temperature for about sevendays, into films having a thickness of about 20 mil to about 60 mil. Thefilms were cut into one inch squares. After seven days, the assemblieswere exposed to the conditions specified in the tables below. After thatexposure the respective solvents were evaluated for residual materials.As indicated, the amount of residual material was less than 10 gm/in²regardless of the solvent and temperature used. The total amount ofresidual material, as shown in Table XI, was then dissolved in hotchloroform and filtered. The results from this test, after evaporationof the chloroform, was further evaluated for residual material, as shownin Table XII. The results shown in both Tables XI and XII indicate thatvery little uncured or unreacted material remains and thus the potentialfor migration or contamination of surrounding items is negligible.

TABLE XI Solvent Resistance Test I Total Residual Material, mg/in²Water, Heptane, 8% Ethanol, Inventive 30 min. 2 hr 2 hr Sample No.Composition @ 212° F. @ 150° F. @ 150° F. 1 C 2.36 0.076* 4.54 2 C 4.360.096* 5.74 3 C 4.12 0.076* 5.26 4 D 6.02 0.260* 6.30 5 D 5.44 0.344*9.38 6 D 5.78 0.304* 6.92

TABLE XII Solvent Resistance Test II Total Residual Material, mg/in²Water, Heptane, 8% Ethanol, Inventive 30 min. 2 hr 2 hr Sample No.Composition @ 212° F. @ 150° F. @ 150° F. 1 C 0.180 0.064* 2.00 2 C 1.880.052* 3.20 3 C 2.42 0.088* 1.98 4 D 2.14 0.184* 0.52 5 D 1.50 0.240*2.24 6 D 3.28 0.228* 1.66

Example IX

Compositions C and D were also tested for their threadlocking strengthon non-ferrous (passive) substrates, as compared to commerciallyavailable Henkel 242 threadlocker. The results, shown below in TableXIII, indicate significantly greater breakaway and prevail values thanthe commercial liquid threadlocker. This demonstrates excellent strengthon substrates in which conventional anaerobics have difficulty achievinghigh strength curves. Thus, the substrate insensitivity of the inventivecompositions is clearly shown in these tests.

TABLE XIII Threadlocker Adhesives Inventive Inventive Properties ControlComposition C Composition D Breakaway strength/prevail, in-lbs StainlessN/A 206/67 137/53 Steel Breakloose strength/prevail, in-lbs Stainless43/2 243/64 163/69 Steel Breakaway strength/prevail, in-lbs Regular N/A168/88 N/A Steel Breakloose strength/prevail, in-lbs Regular Steel129/22 249/64 179/50 Breakaway strength/prevail, in-lbs Zinc  93/20198/67 N/A Phosphate Breakloose strength/prevail, in-lbs Zinc 120/19210/56 154/42 Phosphate

1. A dry-to-the-touch curable composition comprising: a polymeric matrixcomprising a material selected from the group consisting of apolyurethane, a polyurea, a polysulfonamide, a polythiourethane andcombinations thereof; and an anaerobically curable component dispersedwithin said polymeric matrix, wherein said polymeric matrix is presentin amounts of about 30% to about 80% by weight of the composition, andthe composition remains non-flowable at temperatures greater than 260°C. up to about 300° C.
 2. The composition of claim 1, further comprisinga moisture cure catalyst.
 3. The composition of claim 1, wherein saidpolymeric matrix comprises a reaction product of a multifunctionaldiisocyanate and a multifunctional alcohol.
 4. The composition of claim1, wherein said polymeric matrix comprises a reaction product of amultifunctional diisocyanate and an amine.
 5. The composition of claim1, wherein said polymeric matrix comprises a reaction product of amultifunctional diisocyanate and a thiol.
 6. The composition of claim 1,further comprising a carrier substrate.
 7. The composition of claim 1,wherein said anaerobically curable component comprises at least one(meth)acrylate monomer and at least one peroxide compound.
 8. Thecomposition of claim 1, wherein the polymeric matrix material is presentin amounts of about 30% to about 80% by weight of the total composition.9. The composition of claim 1, wherein the composition remainsnon-flowable at temperatures greater than 260° C. and up to about 300°C.
 10. A composition comprising: a matrix comprising: (a) the polymericreaction product of: a polyisocyanate reactant and at least one compoundselected from the group consisting of: (i) an alcohol; (ii) an amine;(iii) a thiol; (iv) sulfonamide; and (b) an anaerobically curablecomposition distributed within said matrix.
 11. The matrix of claim 10,wherein said polyisocyanate reactant is selected from the groupconsisting of: monomeric 4,4′-methylene diphenyl diisocyanate, phenyldiisocyanate, toluene diisocyanate, 4,4′-diphenyl diisocyanate,4,4′-diphenylene methane diisocyanate, dianisidine diisocyanate,1,5-naphthalene diisocyanate, 4,4′-diphenyl ether diisocyanate,p-phenylene diisocyanate, 4,4′-dicyclo-hexylmethane diisocyanate,1,3-bis-(isocyanatomethyl)cyclohexane, cyclohexylene diisocyanate,tetrachlorophenylene diisocyanate, 2,6-diethyl-p-phenylenediisocyanate,and 3,5-diethyl-4,4′-diisocyanatodiphenylmethane.
 12. The matrix ofclaim 13, wherein the polyisocyanate is polyamine polyisocyanate. 13.The matrix of claim 10, wherein said alcohol is selected from the groupconsisting of: polyethylglycol ethers, polyesters, polyethers,polybudadienes, castor oil, glycerin, polyethylene glycol, etherdiol,ethylene glycol, caprolactone polyols and combinations thereof.
 14. Thematrix of claim 10, wherein said anaerobically curable compositioncomprises a (meth)acrylate monomer and a peroxide compound.
 15. Thematrix of claim 10, wherein said matrix comprises a moisture curablecomposition comprising a material selected from a group consisting of apolyurethane, a polyurea, a polyureaurethane, a polysulfonamide, apolythiourethane and combinations thereof.
 16. A product comprising: acarrier substrate; and a coating on said substrate comprising: apolymeric matrix comprising a material selected from a group consistingof a polyurethane, a polyurea, a polysulfonamide, a polythiourethane andcombinations thereof; and an anaerobically curable component presentwithin said matrix.
 17. The product of claim 16, wherein said substratecomprises a plastic, a cellulosic material, cotton, polyurethane orpolytetrafluoroethylene.
 18. The product of claim 16, wherein saidsubstrate is in the form of a tape, a string or a sheet.
 19. An articleof manufacture comprising: a threaded member at least partially coatedwith a dry-to-the-touch composition comprising a polymeric matrixselected from the group consisting of a polyurethane, a polyurea, apolythiourethane and combinations thereof and having an anaerobicallycurable component distributed therein.
 20. The article of manufacture ofclaim 19, wherein said threaded member is a bolt or a nut.
 21. Thearticle of manufacture of claim 19, wherein said threaded member is apipe.
 22. The article of manufacture of claim 19, wherein said polymericmatrix comprises a material selected from a group consisting of apolyurethane, a polyurea, a polysulfonamide, an epoxy and combinationsthereof.
 23. The article of manufacture of claim 19, wherein saidpolymeric matrix comprises a moisture curable composition.
 24. Anarticle of manufacture comprising a preformed gasket comprising adry-to-the-touch polymer matrix having an anaerobically curablecomponent distributed therein.
 25. A method of preparing an article ofmanufacture comprising: (a) providing a threaded member; (b) at leastpartially coating said threaded member with a dry-to-the-touch polymericmatrix having an anaerobically curable component distributed therein.26. A method of assembling threaded parts comprising: (a) providing afirst threaded member; (b) providing a second threaded member capable ofmatingly engaging said first threaded member; at least one of said firstand second threaded members being at least partially coated with adry-to-the-touch composition comprising a polymeric matrix and aanaerobically curable component distributed therein; (c) matinglyengaging said first and second threaded parts and permitting thecomposition to anaerobically cure therebetween.